My favorite golf hole: A picturesque, and punishing, par 3 along the bay on Long Island

This is the latest in a multi-part series where our writers and editors wax poetic about their all-time favorite golf hole. Look for more entries throughout the holiday season. Enjoy!

The par-3 5th hole on the Blue Course at Timber Point Golf Club, aka “Gibraltar,” has long been my nemesis. It features an elevated green, 188 yards from the middle tees, that overlooks the Great South Bay from Great River, Long Island. Depending on the wind, Gibraltar can play anywhere from 160 to 220 yards. Somehow the wind never seems to blow in my favor.

If you follow any Long Island golfers on social media who play the public-course circuit, there’s a strong chance you’ve seen a photo or video from Gibraltar land on their feed. Even if you prefer to tuck your phone away during a round, you can’t help but pull it out upon reaching the green. As someone who works in social media, I can promise that this hole will bring you a lot of likes.

From the moment I wheel into Timber Point, I gauge which way the wind will blow on Gibraltar. It’s always on my mind. To me, the hole is the epitome of Long Island golf. There’s fescue, salt-water spray crashing against the back of the green, sweeping views of the bay and remnants of crab and fish that the birds left behind. You always leave knowing that you earned your score – no matter what it was.

Without fail, I struggle to select a club every single time I arrive at the tee box. It’s my equivalent to asking my girlfriend what she wants for dinner. I always insist my playing partners go first on this hole, and not because I’m overly polite – I want to use them as my test subjects before selecting one of the four or so clubs I’ve narrowed it down to.

I can’t even estimate how many times I’ve played Timber Point and Gibraltar. I can estimate that I’ve watched perfectly struck tee shots come up agonizingly short no less than a million times, give or take a few.

For me, a Gibraltar par is a rarity and birdies are like Haley’s Comet. Despite my struggles, it continues to be my favorite to play. Maybe I like the challenge. Or, maybe I just like getting my ass kicked. It’s hard to say.

I’ve never made a hole-in-one in my life. If the golf gods are reading this, I would love nothing more than to accomplish that feat on Gibraltar. Rather than retire on top, I know I’d still keep coming back to launch more tee shots into the bay.

See you in the spring, Gibraltar, with my 3-wood, hybrid, 5- and 6-iron in hand.